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Portland

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Portland Flights as Low as $155

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$155 Roundtrip, found 2 hours ago
$155
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $155 found 2 hours ago
Breeze Airways
Thu, Dec 3 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$169 Roundtrip, found 18 hours ago
$169
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $169 found 18 hours ago
Frontier Airlines
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$170 Roundtrip, found 2 hours ago
$170
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $170 found 2 hours ago
Frontier Airlines
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 6 hours ago
$174
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $174 found 6 hours ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$184 Roundtrip, found 2 hours ago
$184
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $184 found 2 hours ago
Breeze Airways
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$206 Roundtrip, found 1 hour ago
$206
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $206 found 1 hour ago
Frontier Airlines
Wed, Oct 7 - Wed, Oct 14
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Oct 7 from Luis Munoz Marin Intl. to Bradley Intl., returning Wed, Oct 14, priced at $206 found 1 day ago
American Airlines
Tue, Oct 20 - Tue, Oct 27
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 20 from Luis Munoz Marin Intl. to Bradley Intl., returning Tue, Oct 27, priced at $230 found 3 days ago
Southwest Airlines
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$243 Roundtrip, found 6 hours ago
$243
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Dec 5 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $243 found 6 hours ago
JetBlue Airways
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $247 found 2 hours ago
Delta
Tue, Oct 27 - Sat, Nov 14
JAX
Jacksonville Intl.
BDL
Bradley Intl.
$254 Roundtrip, found 5 hours ago
$254
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Oct 27 from Jacksonville Intl. to Bradley Intl., returning Sat, Nov 14, priced at $254 found 5 hours ago
Bargain Flight
Fri, Oct 2 - Mon, Oct 5
MCO
Orlando Intl.
BDL
Bradley Intl.
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Oct 2 from Orlando Intl. to Bradley Intl., returning Mon, Oct 5, priced at $256 found 1 day ago
Delta
Mon, Oct 5 - Wed, Oct 14
JAX
Jacksonville Intl.
BDL
Bradley Intl.
$260 Roundtrip, found 3 days ago
$260
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Oct 5 from Jacksonville Intl. to Bradley Intl., returning Wed, Oct 14, priced at $260 found 3 days ago
Breeze Airways
Mon, Sep 28 - Mon, Sep 28
JAX
Jacksonville Intl.
HVN
Tweed - New Haven Regional
$283 Roundtrip, found 1 day ago
$283
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Sep 28 from Jacksonville Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $283 found 1 day ago
Avelo Airlines
Fri, Dec 4 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$286 Roundtrip, found 1 hour ago
$286
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Fri, Dec 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 6, priced at $286 found 1 hour ago
Southwest Airlines
Thu, Nov 19 - Sat, Dec 5
DAL
Love Field
BDL
Bradley Intl.
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Nov 19 from Love Field to Bradley Intl., returning Sat, Dec 5, priced at $347 found 1 day ago

Cheap Flights to Portland

Fall in love at first flight with your vacation to Portland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Portland on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Portland, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Portland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Portland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HFD airport.

What is the cheapest month to fly to Portland?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Portland are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Portland?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Portland.

What airport is best to fly into Portland?

When you’re planning your trip to Portland, convenience is the name of the game. Luckily, Portland Tweed - New Haven Regional Airport is nearby so you can deplane and get going on checking off everything on your Portland must-do list.

How much are flights to Portland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Portland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $155, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Portland?

The trick to saving a stack of cash on your flight to Portland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $155 right now, why wait?

Portland Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$155

Last Minute Hotel Deals in Portland

Solano Inn

Solano Inn

2.5 out of 5
1503 Portland-Cobalt Rd Portland CT
Stay at this hotel in Portland. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Arrigoni Winery and Chris Cote's Toptracer Golf ...
8.4/10 Very Good! (277 reviews)
"Feel in love with this place! We were on route back from big e needed somewhere to stay with our baby as well and got a great price on the suite! It’s spacious inviting well maintained and had a super comfy bed! Shower was fantastic good pressure spacious and plenty of hot water! Would definitely ..."

Reviewed on Sep 24, 2026

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Solano Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
7.4/10 Good! (1,541 reviews)
"Couldn't even visit. Wanted to get a refund to book for another date. I booked the hotel for my aunt's funeral but it got pushed forward. The staff and manager had no sympathy and refused to give me a refund. Almost $300 wasted for nothing."

Reviewed on Sep 24, 2026

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The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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Holiday Inn Express Southington by IHG
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
Stay at this cabin in East Haddam. Enjoy free parking, patios, and climate control. Popular attractions Machimoodus State Park and Amasa Day House are located ...
9.4/10 Exceptional! (191 reviews)
"Highly recommend it it was 10/10"

Reviewed on Sep 20, 2026

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Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
351 Pitkin Steet East Hartford CT
Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,222 reviews)
"I had a wonderful stay at the Hampton Inn & Suites Hartford/East Hartford. The hotel was comfortable, clean, and welcoming, and I really enjoyed my time there. The staff was friendly and helpful, the atmosphere was pleasant and relaxing, and everything I needed was conveniently available. I especially ..."

Reviewed on Sep 24, 2026

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Hampton Inn & Suites Hartford/East Hartford
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd Hartford CT
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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Best Western Hartford Hotel & Suites
Ramada by Wyndham Hartford North / Bradley Airport

Ramada by Wyndham Hartford North / Bradley Airport

2.5 out of 5
383 South Center St Windsor Locks CT
Stay at this hotel in Windsor Locks. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Oliver Ellsworth Homestead and Connecticut ...
6.2/10 (1,001 reviews)
"It was honestly very scary staying at this hotel. I am stunned that Hotels.com would even recommend or consider this property for their guests. The entire place looked and felt like an abandoned hotel. It was so dirty and uncomfortable that we didn’t even feel comfortable taking our clothes off to ..."

Reviewed on Sep 24, 2026

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Ramada by Wyndham Hartford North / Bradley Airport
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
201 Washington Avenue North Haven CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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Clarion Inn North Haven - New Haven North
See all 721 properties in Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.